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Published on: September 25, 2017
Efficient synthesis of pillar[5]quinone for rapid identification of aromatic nitro explosives
Yue-Yi Zhang1, Lu Wang1, Jiabin Wu1
1Academy of Interdisciplinary Studies on Intelligent Molecules, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University Tianjin 300387 P. R. China jbwu@tjnu.edu.cn zzy@tjnu.edu.cn hxxyly@tjnu.edu.cn cjli@shu.edu.cn.
Abstract:
An efficient synthesis of pillar[5]quinone (Q5) is reported for the rapid identification of aromatic nitro explosives. A record-high synthetic yield of 96% on a gram scale for Q5 can be achieved via a two-step reaction process involving the demethylation of pillar[5]arene to hydroxypillar[5]arene, followed by oxidation with Oxone to form Q5. In addition, by modifying amino silicon spheres with Q5 to prepare a stationary phase material (Q5-Sil) for high-performance liquid chromatography (HPLC), efficient separation of eight typical aromatic nitro-explosives was achieved using a single column. The underlying mechanism of the separation of aromatic nitro-explosives in the Q5-Sil-packed column resulted from dipole-dipole interactions, hydrophobic effects, and steric factors between Q5 and analytes. This work achieved the quantitative synthesis of Q5, established a novel method of macrocyclic modification of chromatographic column stationary phase materials, and provided a mixed mechanism for the HPLC-based separation of aromatic nitro-explosives, expanding the interdisciplinary applications of macrocyclic supramolecular chemistry in the field of analytical separation science.
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